Pyridine → HCID 54537893, compound

HRID 1805903Notes

Reaction equation

HRID 1805903 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].N1C=CC=CC=1.[OH:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][Br:18])=[CH:14][CH:13]=1>C(Cl)Cl.O>[C:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][Br:18])=[CH:14][CH:13]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 842214-(2-Bromoethyl)phenol

Product 1

HCID 54537893HCID 54537893, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (2.01 g, 1.82 mL. 25.6 mmol) was added to a stirred solution of pyridine (2.02 g, 2.07 mL, 25.6 mmol) and 4-hydroxyphenethyl bromide (856.5 mg, 4.26 mmol) in dry CH2Cl2 (17 mL) and the reaction was stirred at room temperature for 2 h. The reaction mixture was diluted with water (20 mL) and extracted with CH2Cl2 (2×40 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford 4-(2-bromoethyl)phenyl acetate. 1H NMR (500 MHz, CHCl3): δ 7.22 (d, J=8.3 Hz, 2 H); 7.04 (d, J=8.3 Hz, 2 H); 3.55 (t, J=7.6 Hz, 2 H); 3.16 (t, J=7.6 Hz, 2 H); 2.29 (s, 3 H).

Workup

  1. extractionextracted with CH2Cl2 (2×40 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f768dfa27c554c5b94fcf5b518b86ed4
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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